Anisole → 1-(1-aminoisoquinoline-7-carbonyl)-2'-tert-butyl-4',6'-dihydrospiro[piperidine-4,5'-pyrazolo[3,4-c]pyridin]-7'(2'H)-one

HRID 881010Notes

Reaction equation

HRID 881010 reaction equation
[C:1]([N:5]1[CH:13]=[C:12]2[C:7]([C:8](=[O:41])[NH:9][C:10]3([CH2:18][CH2:17][N:16]([C:19]([C:21]4[CH:30]=[C:29]5[C:24]([CH:25]=[CH:26][N:27]=[C:28]5[NH:31]CC5C=CC(OC)=CC=5)=[CH:23][CH:22]=4)=[O:20])[CH2:15][CH2:14]3)[CH2:11]2)=[N:6]1)([CH3:4])([CH3:3])[CH3:2].C1(OC)C=CC=CC=1>FC(F)(F)C(O)=O>[NH2:31][C:28]1[C:29]2[C:24](=[CH:23][CH:22]=[C:21]([C:19]([N:16]3[CH2:17][CH2:18][C:10]4([NH:9][C:8](=[O:41])[C:7]5=[N:6][N:5]([C:1]([CH3:2])([CH3:3])[CH3:4])[CH:13]=[C:12]5[CH2:11]4)[CH2:14][CH2:15]3)=[O:20])[CH:30]=2)[CH:25]=[CH:26][N:27]=1

Participants

4

Reactant 2

HCID 7519AnisoleHCID 674915152'-tert-butyl-1-(1-(4-methoxybenzylamino)isoquinoline-7-carbonyl)-4',6'-dihydrospiro[piperidine-4,5'-pyrazolo[3,4-c]pyridin]-7'(2'H)-one

Product 1

HCID 675165271-(1-aminoisoquinoline-7-carbonyl)-2'-tert-butyl-4',6'-dihydrospiro[piperidine-4,5'-pyrazolo[3,4-c]pyridin]-7'(2'H)-oneYield 32.2%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of 2′-tert-butyl-1-(1-(4-methoxybenzylamino)isoquinoline-7-carbonyl)-4′,6′-dihydrospiro[piperidine-4,5′-pyrazolo[3,4-c]pyridin]-7′(2′H)-one (28 mg, 0.051 mmol) in trifluoroacetic acid (0.51 mL) was added anisol (8.3 μL, 0.076 mmol). The reaction was heated to 65° C. and stirred for 19 hours. The reaction was concentrated. Purification by reversed-phase HPLC gave the title compound (7.1 mg, 32%). +ESI (M+H) 433.2; HPLC retention time 1.79 minutes (Method A).

Workup

  1. concentrationThe reaction was concentrated
  2. customPurification by reversed-phase HPLC

Sources & evidence

ORD record
ord-943b8d328b104d939e814a79267e3a07
Source dataset
uspto-grants-2015_03
Patent number
US08993586B2

Reaction notes

Loading…